Windsor County Vacation Packages

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Your Windsor County Vacation

With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.

Top vacation destinations in Windsor County

A wooden covered bridge with a sign reading 'Slippery When Wet' and a sign above the entrance that says 'Michael's Bridge.'
FlightsFlightsHotelsHotels

Woodstock

Woodstock

Top Windsor County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was CA $1,892, price is now CA $1,585 per person
CA $1,585
per person
Dec 29 - Jan 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.2/10 Wonderful! (130 reviews)
Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 nights because of the difficulty of the stairs… It was however nice if no handicaps

Reviewed on Oct 8, 2026

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was CA $3,187, price is now CA $2,488 per person
CA $2,488
per person
Dec 24 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (147 reviews)

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
Save 100% on your flight
Price was CA $5,848, price is now CA $4,670 per person
CA $4,670
per person
Dec 24 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (138 reviews)

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was CA $2,620, price is now CA $2,174 per person
CA $2,174
per person
Dec 29 - Jan 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.8/10 Excellent! (1,004 reviews)
We booked a deluxe suite, and it was fantastic — basically a full one-bedroom apartment with a kitchen equipped with all the essentials, including a washing machine and dryer. The location is quiet and peaceful, and the property itself is clean, cozy, and well-maintained. The hotel also has great amenities like a pool, gym, and hot tub — unfortunately, we didn't get a chance to use them this time, but it's a wonderful bonus to have! There were only two small issues: it was a bit tricky to find our room at first since it was located in the far wing of the building, and the heater was rather hard to adjust. Aside from that, our stay was wonderful. We love staying at this hotel and will definitely be back again!

Reviewed on Nov 14, 2026

Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Save 100% on your flight
Price was CA $6,327, price is now CA $5,338 per person
CA $5,338
per person
Dec 24 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
7.8/10 Good! (23 reviews)

Windsor County Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $469 per night from Nov 30 to Dec 1
CA $469
CA $579 total
Nov 30 - Dec 1
includes taxes & fees
Woodstock Inn & Resort
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
The price is CA $272 per night from Nov 19 to Nov 20
CA $272
CA $330 total
Nov 19 - Nov 20
includes taxes & fees
Jackson Gore Village, A Vail Resorts Property
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $186 per night from Dec 6 to Dec 7
CA $186
CA $233 total
Dec 6 - Dec 7
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Filthy carpets and shower curtains."

Reviewed on Nov 13, 2026

On The River Inn
See all 1,385 properties in Windsor County
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Windsor County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Windsor County from just CA $1,585. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Windsor County?
You'll save a ton of money if you bundle your hotels, car rentals and flights into a Windsor County travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels all over the world, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Windsor County?
Okemo Mountain Resort is one of the key things that lures people to Windsor County, so it makes perfect sense that many decide to book their hotel in Ludlow.
What are the top hotels in Windsor County?
When it comes to hotels in Ludlow, Super 8 by Wyndham White River Junction and Holiday Inn Express Hotel & Suites White River Junction, an IHG Hotel are two terrific options. If you're spending time in Plymouth, Hotel Coolidge and White River Inn and Suites will make you feel right at home.
How far in advance should I book my Windsor County vacation?
It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper flight only weeks before their intended journey.
What does an Expedia Windsor County travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Windsor County? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Windsor County travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even glamping tents!
Can I choose my airline with a Windsor County Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from across the world. With so many choices, finding the ideal carrier to fly you to Windsor County will be a snap.
If I'm not able to travel, can I cancel my Windsor County vacation package?
We get it — unexpected stuff happens. If you've locked in a Windsor County vacation package and need to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

Stay near popular Windsor County attractions

A snow-covered ski resort with ski lifts, buildings, and a mountain backdrop.

Okemo Mountain Resort

9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.